Lessons for Entrepreneurs from Trump’s Political Ascendance

No, I’m not sure President-elect Trump – I have to get used to saying that! – is the greatest entrepreneur, and I don’t propose that we examine how he built a real estate empire to get some tips as would-be entrepreneurs.

Rather, his surprise US Presidential election victory is worth examining, not as any form of endorsement at all, but as an arms-length observation. The more I think about it – and of course hindsight is 20/20 – the more I feel that Trump’s political ascendance replays a story that is as old as the hills to entrepreneurs, but is worth a reminder, nonetheless.

First, there is a “market” that this novice political entrepreneur recognized that he was serving: the market for those hungry for a new political message. This market had expanded. Why? Because the excesses of the past, the rampant inequality it has engendered in America, and the failure of the system to bring those perceived to be at fault to account, had alienated a lot of people. These folks were usually disengaged from politics. This time, they were anything but. They came out in force. And Trump sensed their anger.

Of course, claiming that one is an ‘outsider’ seeing things anew is de rigueur in Washington today. George W. Bush ran as an outsider, Obama was a young senator from Illinois, and Ted Cruz insisted he’d bust up Washington. But Trump – never holding public office, never serving in armed forces, proudly displaying ignorance about essential aspects of the job – really is new to politics.

Why didn’t political insiders – whether the dynasties of Clinton or Bush, or younger ‘newbies’ like senators Rubio or Cruz – see this expanding market? It’s the same reason that incumbent companies don’t see new challenges coming. They underestimate and discount new competition, overestimate their own strengths, and are blind to new technologies. All of this happened in America’s political market.

The insider politicians had their own political networks. These have strengths, of course, but they also create blind spots. They create echo chambers, where the supporters all talk to each other, and not to others. It’s easy to imagine that you’re deluded about your ability to get a true picture of what’s going on when you only hear supporting voices day-in-and-day-out.

What about the watchdog media, were they not presenting the entire picture? It appears not. Much ink has been spilled on it, basically pointing to the polarization of existing physical and online media – the creation of so-called conservative and progressive echo-chambers where people just kept talking past each other. Neither side got a full picture.

I’ll only add that, as the market expanded to middle and small town America, mainstream physical media was withdrawing its physical presence – its bureaus and feet-on-the-street – in exactly those places, driven by relentless cost pressure in their own industry. Therefore, their ability to accurately describe what was happening in the places that newly mattered was increasingly untenable anyway.

Meanwhile, Trump was relatively immune to this issue since he unabashedly discounted traditional media, cultivating a Twitter-led approach to communicating with the new market directly.

Here again is part of the ‘normal’ story of new entrepreneurs, embracing new technologies more readily than incumbent enterprises. Incidentally, as this Forbes piece suggests, there seems to have been quite a savvy data operation backing the Trump campaign, led by his son-in-law Jared Kushner.

So, this reminds entrepreneurs of two lessons that are as old as the hills:

(1) First, seek out new voices widely to inform your approach, preferably from folks different from yourself, so that you don’t box yourself into an echo-chamber.

(2) Second, while you can’t realistically respond to every new technology that comes along – that would be paralyzing in itself – you can remind yourself that your existing models always create their own blind spots. Forewarned, as they say, is forearmed.

Of course, going forward, this applies to Trump as well. His intuition in tapping into the disenfranchised won’t protect him if he falls into his own echo-chamber. Then, he’ll suffer the same way that Clinton et al did this time around.